As the year wraps up, our host Tim Pope highlights key planning reminders for pilots: open enrollment choices, tax strategies, 401(k) adjustments, and life changes like marriage, divorce, child birth, or buying a new home. He also covers Roth conversions, gain harvesting, FSA timing, and estate document updates.

What You'll Learn from This Episode

• Open Enrollment Considerations: What to review before re-electing benefits, especially if your airline changed providers or you’ve had a major life event.
• Life Transitions and Benefits: How marriage, divorce, childbirth, or military retirement can affect your insurance, estate, and legal plan decisions.
• 401(k) Strategy: How to check your contribution progress, set your 2026 target, and re-evaluate Roth vs. traditional deferrals.
• Roth Conversions and Tax Bracket Planning: Why timing and bracket awareness matter when converting pre-tax dollars.
• Tax Gain Harvesting: How a low-income year might open a window to reset capital gains with little to no tax cost.
• Backdoor Roth Contributions: What deadlines actually apply and how to execute this multi-step move.
• FSA and Dependent Care Planning: Ways to prepare for upcoming expenses and reduce taxable income.
• Withholding Checkups: How to avoid surprises (or big refunds) in April by making Q4 adjustments now.
• Balancing Values and Financial Planning: Why it’s okay to spend money when it aligns with what matters to you, and how Tim applied that to a recent family mountain biking expense.

Resources:

Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

This episode is sponsored by: Beacon Relocation

Beacon Relocation is a real estate firm helping pilots and air traffic controllers save money on their real estate transactions. By tapping into their network of over 1500 real estate agents across the country, pilots can save 20% of the real estate agent’s commission towards your closing cost on the sale or purchase of your home. Visit https://www.beaconrelocation.com/ to learn more.

Timothy P. Pope is a Certified Financial Planner™and principal owner of 360 Aviation Advisors, LLC (“360 Aviation Advisors”), a registered investment advisory firm. Investment advisory services are provided through 360 Aviation Advisors, in its separate and individual capacity as a registered investment adviser. Podcast episodes are provided through Pilot’s Portfolio, in its separate and individual capacity.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

You've probably heard the saying, "The best day of your life is when you sell it": and no, we're not talking about boats. We're talking about self managed rental properties. In this episode, Tim is joined by Trevor Flor, Navy veteran, former Delta pilot, and now a real estate investment advisor specializing in DSTs (Delaware Statutory Trusts) and 1031 exchanges at Aimpoint Investments. Trevor breaks down how 1031 exchanges really work, why DSTs were created, and how this is one potential approach to consider.

What You'll Learn from This Episode

• 1031 Exchanges Demystified: How selling investment property can be one potential approach to consider, depending on individual circumstances.
• DSTs as a Solution: Why Delaware Statutory Trusts were created, how they enable fractional ownership, and when they work best.
• Three DST Strategies: Using DSTs as a primary, backup, or complementary approach depending on your goals and exchange value.
• Timeline Rules That Matter: The 45-day identification window and 180-day close deadline - and what happens if you miss them.
• Partial Exchanges and Cash Boot: Can you peel off cash from a sale and still do a 1031? Yes, but at what cost?
• Accredited Investor Requirements: What qualifies you for DST access and what documentation you'll need.
• Types of DST Properties: From multifamily and industrial to storage, hotels, and more - what's available and how it's selected.

Resources:

Trevor Flor’s firm, Aimpoint Investments: www.aimpointinvest.com
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

This episode is sponsored by: Beacon Relocation

Beacon Relocation is a real estate firm helping pilots and air traffic controllers save money on their real estate transactions. By tapping into their network of over 1500 real estate agents across the country, pilots can save 20% of the real estate agent’s commission towards your closing cost on the sale or purchase of your home. Visit https://www.beaconrelocation.com/ to learn more.

Timothy P. Pope is a Certified Financial Planner™and principal owner of 360 Aviation Advisors, LLC (“360 Aviation Advisors”), a registered investment advisory firm. Investment advisory services are provided through 360 Aviation Advisors, in its separate and individual capacity as a registered investment adviser. Podcast episodes are provided through Pilot’s Portfolio, in its separate and individual capacity.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

In this episode, Tim asks the question many pilots hear in the cockpit: Is your 401(k) a scam? He walks through why 401(k)s exist, how they replaced pensions, and what today’s airline plans actually offer: contribution mechanics, investment menus, legal protections, and employer contributions specific to the majors. Tim also shares a listener email requesting a cargo-carrier disability deep-dive and invites other cargo pilots to weigh in.

What You'll Learn from This Episode

• Pensions vs. 401(k)s: Why pensions faded (PBGC oversight, funding issues)
  and how 401(k)s became the primary retirement tool.
• How Airline 401(k)s Work: Salary deferrals: pre-tax and Roth, after-tax
  contributions, investment menus, brokerage window.
• Contribution Limits & Employer Money: What “up to $70,000 per year”
  includes: deferral, after-tax non-Roth, NEC; why big plans mean lower-cost
  funds.
• Ownership & Vesting: Immediate vesting when dollars hit your account: what it means if you stay or leave.
• Legal Protections & Risks: 401(k)s protected from creditors, suits, bankruptcy; IRA and Roth IRA bankruptcy protection to ~$1.7M through 2028; civil-suit rules vary by state; QDROs in divorce are the exception.
• Beneficiaries that Bypass Probate: Keep beneficiaries current to speed
  distributions and reduce taxes.
• What Might Be Coming Next: In August order asks DOL to review alternatives
  in 401(k)s: private equity, private credit, crypto, real estate, digital assets

Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

This episode is sponsored by: Beacon Relocation

Beacon Relocation is a real estate firm helping pilots and air traffic controllers save money on their real estate transactions. By tapping into their network of over 1500 real estate agents across the country, pilots can save 20% of the real estate agent’s commission towards your closing cost on the sale or purchase of your home. Visit https://www.beaconrelocation.com/ to learn more.

Timothy P. Pope is a Certified Financial Planner™and principal owner of 360 Aviation Advisors, LLC (“360 Aviation Advisors”), a registered investment advisory firm. Investment advisory services are provided through 360 Aviation Advisors, in its separate and individual capacity as a registered investment adviser. Podcast episodes are provided through Pilot’s Portfolio, in its separate and individual capacity.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.